Iron Man 3
The third Iron Man movie came after the first Avengers, which means it’s the only movie with the name of Tony Stark’s superhero alter ego in the title that gets to really reckon with the bigger picture. By this point, Tony has seen some shit, fought aliens, and met Norse gods. He’s come a long way since his days as a mere billionaire genius playboy philanthropist. Iron Man 3 paves the way for the sacrifices Tony will have to make in Infinity War and Endgame, exposing the broken core underneath the metal suit exterior. On the other hand, its mishandling of villain the Mandarin is one of the MCU’s most notable misfires, though at least Shang-Chi managed to iron out some of those kinks eight years later. — Kenneth Shepard